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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:26:34 UTC

Update Date

2021-09-23 20:26:34 UTC

HMDB ID

HMDB0302757

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Epimuurolene

Description

Gamma-cadinene, also known as D-G-cadinene or gamma-cadinene, (+)-isomer, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Gamma-cadinene is a wood tasting compound and can be found in a number of food items such as hyssop, lemon balm, sweet orange, and common sage, which makes gamma-cadinene a potential biomarker for the consumption of these food products. Gamma-cadinene can be found primarily in saliva. Chemically, the cadinenes are bicyclic sesquiterpenes. The term cadinene has sometimes also been used in a broad sense to refer to any sesquiterpene with the so-called cadalane (4-isopropyl-1,6-dimethyldecahydronaphthalene) carbon skeleton. Because of the large number of known double-bond and stereochemical isomers, this class of compounds has been subdivided into four subclasses based on the relative stereochemistry at the isopropyl group and the two bridgehead carbon atoms. The name cadinene is now properly used only for the first subclass below, which includes the compounds originally isolated from cade oil. Only one enantiomer of each subclass is depicted, with the understanding that the other enantiomer bears the same subclass name .

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0302757
     RDKit          3D
Epimuurolene
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.6028   -3.3099    0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -2.3452    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5903   -2.5866   -0.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585   -1.7364    0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1384   -0.3371    0.4483 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2604    0.6323    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025    2.0329    0.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4718    0.1777    1.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649   -0.0422   -0.3920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5476    1.2964   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815    1.7390   -0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1863    3.1544   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465    0.7782    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575   -0.5385   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1756   -0.9336    0.2162 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3434   -4.3721    0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5767   -3.0860    0.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5289   -2.5694   -1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8329   -3.6574   -0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4445   -1.5706   -0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389   -2.2444    0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114   -0.4368    1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183    0.6617   -0.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9300    2.1150    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1272    2.7500   -0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6283    2.3570    1.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441   -0.6143    0.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2193   -0.0920    2.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1507    1.0551    1.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1458   -0.4385   -1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0998    2.0996   -0.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6080    3.5593    0.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3947    3.7995   -0.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0484    3.2310   -1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8543    1.1033   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    0.5787    1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -0.2566   -1.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2689   -1.2820   -0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763   -0.6715    1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15  2  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  1
  6 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  6
 10 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  1
M  END


  Mrv0541 02241219172D          

 17 18  0  0  0  0            999 V2000
   -0.3575    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -0.2062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3575    0.6188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0725    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725   -0.6187    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0725   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    1.4438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -1.0312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 15  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
  6 16  1  6  0  0  0
  5 17  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0302757

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCC(C)=C[C@@]1([H])[C@@H](CCC2=C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13-15H,4-8H2,1-3H3/t13-,14-,15-/m0/s1

> <INCHI_KEY>
WRHGORWNJGOVQY-KKUMJFAQSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
26.261107333935485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4aR,8aR)-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

> <ALOGPS_LOGP>
4.48

> <JCHEM_LOGP>
4.506281368000001

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
67.5259

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-gamma-cadinene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302757
     RDKit          3D
Epimuurolene
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.6028   -3.3099    0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -2.3452    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5903   -2.5866   -0.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585   -1.7364    0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1384   -0.3371    0.4483 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2604    0.6323    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025    2.0329    0.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4718    0.1777    1.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649   -0.0422   -0.3920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5476    1.2964   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815    1.7390   -0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1863    3.1544   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465    0.7782    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575   -0.5385   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1756   -0.9336    0.2162 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3434   -4.3721    0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5767   -3.0860    0.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5289   -2.5694   -1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8329   -3.6574   -0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4445   -1.5706   -0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389   -2.2444    0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114   -0.4368    1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183    0.6617   -0.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9300    2.1150    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1272    2.7500   -0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6283    2.3570    1.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441   -0.6143    0.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2193   -0.0920    2.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1507    1.0551    1.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1458   -0.4385   -1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0998    2.0996   -0.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6080    3.5593    0.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3947    3.7995   -0.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0484    3.2310   -1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8543    1.1033   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    0.5787    1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -0.2566   -1.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2689   -1.2820   -0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763   -0.6715    1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15  2  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  1
  6 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  6
 10 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.667   1.925   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.999   1.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.999  -0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.667  -1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.667   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.002   1.925   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.334   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.334  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.002  -1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.002  -2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.667  -3.465   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.002   3.465   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.334  -3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.334  -1.155   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       0.667   2.695   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.667  -1.925   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10   17                                             
CONECT    6    1    5    7   16                                             
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    5    9   11                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11                                                            
CONECT   13    7                                                            
CONECT   14   11                                                            
CONECT   15    3                                                            
CONECT   16    6                                                            
CONECT   17    5                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0302757
HETATM    1  C1  UNL     1      -1.603  -3.310   0.335  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.778  -2.345   0.026  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.590  -2.587  -0.528  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.658  -1.736   0.056  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.138  -0.337   0.448  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.260   0.632   0.372  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.902   2.033   0.791  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.472   0.178   1.171  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.065  -0.042  -0.392  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.548   1.296  -0.496  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.782   1.739  -0.202  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.186   3.154  -0.340  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.847   0.778   0.263  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.457  -0.538  -0.449  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.176  -0.934   0.216  1.00  0.00           C  
HETATM   16  H1  UNL     1      -1.343  -4.372   0.208  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.577  -3.086   0.731  1.00  0.00           H  
HETATM   18  H3  UNL     1       0.529  -2.569  -1.628  1.00  0.00           H  
HETATM   19  H4  UNL     1       0.833  -3.657  -0.263  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.445  -1.571  -0.706  1.00  0.00           H  
HETATM   21  H6  UNL     1       2.139  -2.244   0.915  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.811  -0.437   1.501  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.618   0.662  -0.712  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.930   2.115   1.274  1.00  0.00           H  
HETATM   25  H10 UNL     1       2.127   2.750  -0.015  1.00  0.00           H  
HETATM   26  H11 UNL     1       2.628   2.357   1.625  1.00  0.00           H  
HETATM   27  H12 UNL     1       4.044  -0.614   0.627  1.00  0.00           H  
HETATM   28  H13 UNL     1       3.219  -0.092   2.201  1.00  0.00           H  
HETATM   29  H14 UNL     1       4.151   1.055   1.223  1.00  0.00           H  
HETATM   30  H15 UNL     1       0.146  -0.439  -1.436  1.00  0.00           H  
HETATM   31  H16 UNL     1       0.100   2.100  -0.883  1.00  0.00           H  
HETATM   32  H17 UNL     1      -2.608   3.559   0.626  1.00  0.00           H  
HETATM   33  H18 UNL     1      -1.395   3.799  -0.736  1.00  0.00           H  
HETATM   34  H19 UNL     1      -3.048   3.231  -1.062  1.00  0.00           H  
HETATM   35  H20 UNL     1      -3.854   1.103  -0.023  1.00  0.00           H  
HETATM   36  H21 UNL     1      -2.738   0.579   1.348  1.00  0.00           H  
HETATM   37  H22 UNL     1      -2.292  -0.257  -1.520  1.00  0.00           H  
HETATM   38  H23 UNL     1      -3.269  -1.282  -0.340  1.00  0.00           H  
HETATM   39  H24 UNL     1      -1.176  -0.672   1.307  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3   15
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6    9   22
CONECT    6    7    8   23
CONECT    7   24   25   26
CONECT    8   27   28   29
CONECT    9   10   15   30
CONECT   10   11   11   31
CONECT   11   12   13
CONECT   12   32   33   34
CONECT   13   14   35   36
CONECT   14   15   37   38
CONECT   15   39
END

HMDB0302757
     RDKit          3D
Epimuurolene
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.6028   -3.3099    0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -2.3452    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5903   -2.5866   -0.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585   -1.7364    0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1384   -0.3371    0.4483 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2604    0.6323    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025    2.0329    0.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4718    0.1777    1.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649   -0.0422   -0.3920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5476    1.2964   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815    1.7390   -0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1863    3.1544   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465    0.7782    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575   -0.5385   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1756   -0.9336    0.2162 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3434   -4.3721    0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5767   -3.0860    0.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5289   -2.5694   -1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8329   -3.6574   -0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4445   -1.5706   -0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389   -2.2444    0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114   -0.4368    1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183    0.6617   -0.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9300    2.1150    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1272    2.7500   -0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6283    2.3570    1.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441   -0.6143    0.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2193   -0.0920    2.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1507    1.0551    1.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1458   -0.4385   -1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0998    2.0996   -0.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6080    3.5593    0.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3947    3.7995   -0.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0484    3.2310   -1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8543    1.1033   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    0.5787    1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -0.2566   -1.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2689   -1.2820   -0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763   -0.6715    1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15  2  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  1
  6 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  6
 10 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
D-gamma-Cadinene	ChEBI
Epi-muurolene	ChEBI
D-g-Cadinene	Generator
D-Γ-cadinene	Generator
(+)-g-Cadinene	Generator
(+)-Γ-cadinene	Generator
gamma-Cadinene	MeSH
gamma-Cadinene, (+)-isomer	MeSH
gamma-Cadinene, (-)-isomer	MeSH
gamma-Cadinene, (+)-gamma(1)-isomer	MeSH
g-Cadinene	Generator, HMDB
γ-cadinene	Generator, HMDB
1,2,3,4,4a,5,6,8a-octahydro-7-Methyl-4-methylene-1-(1-methylethyl)-(1S,4ar,8ar)-naphthalene	HMDB

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.3511

Monoisotopic Molecular Weight

204.187800768

IUPAC Name

(1S,4aR,8aR)-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

Traditional Name

(+)-gamma-cadinene

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC(C)=C[C@@]1([H])[C@@H](CCC2=C)C(C)C

InChI Identifier

InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13-15H,4-8H2,1-3H3/t13-,14-,15-/m0/s1

InChI Key

WRHGORWNJGOVQY-KKUMJFAQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cadinane sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cadinene (CHEBI:63205 )

Ontology

Not Available

Saliva (HMDB: HMDB0302757)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0302757)

Source

Endogenous

Endogenous (HMDB: HMDB0302757)

Plant

Plant (HMDB: HMDB0302757)

Animal

Animal (HMDB: HMDB0302757)

Exogenous

Food

Food (HMDB: HMDB0302757)

Herb and spice

Herb

Spearmint (FooDB: FOOD00112)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0302757)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0302757)

Cellular process

Cell signaling (HMDB: HMDB0302757)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0302757)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0302757)

Nutrient

Nutrient (HMDB: HMDB0302757)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0302757)

Emulsifier (HMDB: HMDB0302757)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.48	ALOGPS
logP	4.51	ChemAxon
logS	-4.5	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.53 m³·mol⁻¹	ChemAxon
Polarizability	26.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	147.942	32859911
AllCCS	[M+H-H2O]+	144.015	32859911
AllCCS	[M+Na]+	152.648	32859911
AllCCS	[M+NH4]+	151.596	32859911
AllCCS	[M-H]-	156.385	32859911
AllCCS	[M+Na-2H]-	156.953	32859911
AllCCS	[M+HCOO]-	157.676	32859911
DeepCCS	[M-2H]-	187.172	30932474
DeepCCS	[M+Na]+	161.98	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Epimuurolene EI-B (Non-derivatized)	splash10-03dl-7900000000-5735da8a4436cae8d6c5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epimuurolene EI-B (Non-derivatized)	splash10-03dl-7900000000-5735da8a4436cae8d6c5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epimuurolene GC-MS (Non-derivatized) - 70eV, Positive	splash10-01p5-2900000000-a648cf16712606029ec4	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epimuurolene 10V, Negative-QTOF	splash10-0udi-0090000000-dc85480898a0884141d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epimuurolene 20V, Negative-QTOF	splash10-0udi-0190000000-93c533f1913690fe3979	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epimuurolene 40V, Negative-QTOF	splash10-000i-1910000000-cb52feba74ceaddb9360	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epimuurolene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epimuurolene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epimuurolene 40V, Negative-QTOF	splash10-0udi-0590000000-152857a7341cf903230d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epimuurolene 10V, Positive-QTOF	splash10-0a4i-0490000000-2e5ae79ecdfa1abff465	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epimuurolene 20V, Positive-QTOF	splash10-0bta-3920000000-9e57207f76fd77fb69fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epimuurolene 40V, Positive-QTOF	splash10-0gvt-6900000000-1be8491b4d6a6699abcb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epimuurolene 10V, Positive-QTOF	splash10-0a4i-1390000000-dec08090d83090223c29	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epimuurolene 20V, Positive-QTOF	splash10-0a4i-4930000000-d018d03e18bf9231bbfa	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epimuurolene 40V, Positive-QTOF	splash10-0006-9500000000-89d5115efd887002de1b	2021-10-21	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006096

KNApSAcK ID

Not Available

Chemspider ID

4937651

KEGG Compound ID

C20173

BioCyc ID

CPD-8787

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6432404

PDB ID

Not Available

ChEBI ID

63205

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Epimuurolene (HMDB0302757)

MOL for HMDB0302757 (Epimuurolene)

3D MOL for HMDB0302757 (Epimuurolene)

3D SDF for HMDB0302757 (Epimuurolene)

3D-SDF for HMDB0302757 (Epimuurolene)

PDB for HMDB0302757 (Epimuurolene)

3D PDB for HMDB0302757 (Epimuurolene)

SMILES for HMDB0302757 (Epimuurolene)

INCHI for HMDB0302757 (Epimuurolene)

Structure for HMDB0302757 (Epimuurolene)

3D Structure for HMDB0302757 (Epimuurolene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

NMR Spectra